DD249041A5 - Verfahren zur herstellung von 4-androsten-3,17-dion und 1,4-androstadien-3,17-dion - Google Patents
Verfahren zur herstellung von 4-androsten-3,17-dion und 1,4-androstadien-3,17-dion Download PDFInfo
- Publication number
- DD249041A5 DD249041A5 DD86291082A DD29108286A DD249041A5 DD 249041 A5 DD249041 A5 DD 249041A5 DD 86291082 A DD86291082 A DD 86291082A DD 29108286 A DD29108286 A DD 29108286A DD 249041 A5 DD249041 A5 DD 249041A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- dione
- mycobacterium
- androstadiene
- ergosterol
- androstene
- Prior art date
Links
- LUJVUUWNAPIQQI-QAGGRKNESA-N androsta-1,4-diene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 LUJVUUWNAPIQQI-QAGGRKNESA-N 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title 1
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims abstract description 12
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 claims abstract description 12
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims abstract description 12
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 claims abstract description 12
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 claims abstract description 12
- 238000006731 degradation reaction Methods 0.000 claims abstract description 11
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 claims abstract description 10
- 230000015556 catabolic process Effects 0.000 claims abstract description 10
- LUJVUUWNAPIQQI-UHFFFAOYSA-N (+)-androsta-1,4-diene-3,17-dione Natural products O=C1C=CC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 LUJVUUWNAPIQQI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229960005471 androstenedione Drugs 0.000 claims abstract description 9
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- 244000005700 microbiome Species 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 241000187488 Mycobacterium sp. Species 0.000 claims description 6
- 229930182558 Sterol Natural products 0.000 claims description 6
- 150000003432 sterols Chemical class 0.000 claims description 6
- 235000003702 sterols Nutrition 0.000 claims description 6
- 241000187481 Mycobacterium phlei Species 0.000 claims description 5
- 229940055036 mycobacterium phlei Drugs 0.000 claims description 5
- 241000186359 Mycobacterium Species 0.000 claims description 3
- 241000186365 Mycobacterium fortuitum Species 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 2
- 125000002328 sterol group Chemical group 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000187480 Mycobacterium smegmatis Species 0.000 description 4
- 150000003431 steroids Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000193830 Bacillus <bacterium> Species 0.000 description 3
- 241001467578 Microbacterium Species 0.000 description 3
- 241000586779 Protaminobacter Species 0.000 description 3
- 241000187747 Streptomyces Species 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 229920000136 polysorbate Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 241000186063 Arthrobacter Species 0.000 description 2
- 241000186146 Brevibacterium Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 1
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 1
- 241001491638 Corallina Species 0.000 description 1
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000186367 Mycobacterium avium Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- -1 fatty acid esters Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
- C12P33/005—Degradation of the lateral chains at position 17
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/863—Mycobacterium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/863—Mycobacterium
- Y10S435/865—Mycobacterium fortuitum
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853521111 DE3521111A1 (de) | 1985-06-10 | 1985-06-10 | Verfahren zur herstellung von 4-androsten-3,17-dion und 1,4-androstadien-3,17-dion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD249041A5 true DD249041A5 (de) | 1987-08-26 |
Family
ID=6273107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86291082A DD249041A5 (de) | 1985-06-10 | 1986-06-06 | Verfahren zur herstellung von 4-androsten-3,17-dion und 1,4-androstadien-3,17-dion |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5516649A (cs) |
| EP (1) | EP0225892B1 (cs) |
| JP (1) | JPH088876B2 (cs) |
| CS (1) | CS258482B2 (cs) |
| DD (1) | DD249041A5 (cs) |
| DE (2) | DE3521111A1 (cs) |
| HU (1) | HU204574B (cs) |
| WO (1) | WO1986007385A1 (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4679707A (en) * | 1981-06-26 | 1987-07-14 | The Coca-Cola Company | Post-mix beverage dispenser apparatus having front access for loading syrup, CO2 and water |
| US4688701A (en) * | 1981-06-26 | 1987-08-25 | The Coca-Cola Company | Self-contained portable post-mix beverage dispenser apparatus having access for manually loading syrup CO2 and water |
| RU2126837C1 (ru) * | 1997-07-18 | 1999-02-27 | Андрюшина Валентина Александровна | Штамм бактерий mycobacterium smegmatis, используемый для окисления стеринов растительного и животного происхождения до андрост-4-ен-3,17-диона |
| AU8779898A (en) * | 1997-08-11 | 1999-03-01 | Weider Nutrition International, Inc. | Compositions and treatments to reduce side effects of administration of androgenic testosterone precursors |
| US6071714A (en) * | 1998-03-26 | 2000-06-06 | Forbes Medi-Tech, Inc. | Process for the microbial conversion of phytosterols to androstenedione and androstadienedione |
| KR100432054B1 (ko) * | 2001-05-11 | 2004-05-17 | (주)유진사이언스 | 스테롤로부터 4-안드로스텐-3,17-디온/안드로스타-1,4-디엔-3,17-디온으로의 뛰어난 전환능을 가지는 미생물 및 이의 제조방법 |
| CN1639354A (zh) * | 2002-02-01 | 2005-07-13 | 阿克佐诺贝尔公司 | 将植物甾醇发酵制备雄二烯二酮的方法 |
| WO2003070925A2 (en) * | 2002-02-21 | 2003-08-28 | Akzo Nobel N.V. | Identification of 3-ketosteroid 9-alfa-hydroxylase genes and microorganisms blocked in 3-ketosteroid 9-alfa-hydroxylase activity |
| US20070225354A1 (en) * | 2006-03-21 | 2007-09-27 | Eric Marchewitz | Use of dihydrolipoamide for enhancing physical performance |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3684657A (en) * | 1970-05-11 | 1972-08-15 | Searle & Co | Selective microbiological degradation of steroidal 17-alkyls |
| US3759791A (en) * | 1970-12-10 | 1973-09-18 | Searle & Co | Selective microbiological preparation of androst-4-ene-3,17-dione |
| DE2703645C3 (de) * | 1976-03-01 | 1981-11-12 | The Upjohn Co., 49001 Kalamazoo, Mich. | Verfahren zur Herstellung eines Gemischs aus Androsta-1,4-dien-3,17-dion und Androst-4-en-3,17-dion |
| US4293645A (en) * | 1976-03-01 | 1981-10-06 | The Upjohn Company | Process for preparing androsta-1,4-diene-3,17-dione and androst-4-ene-3,17-dione |
| JPS5937078B2 (ja) * | 1981-03-16 | 1984-09-07 | 宇部興産株式会社 | アンドロスト−１，４−ジエン−３，１７−ジオンの醗酵製造方法 |
-
1985
- 1985-06-10 DE DE19853521111 patent/DE3521111A1/de not_active Withdrawn
-
1986
- 1986-06-02 DE DE8686903231T patent/DE3671246D1/de not_active Expired - Lifetime
- 1986-06-02 WO PCT/DE1986/000228 patent/WO1986007385A1/de active IP Right Grant
- 1986-06-02 EP EP86903231A patent/EP0225892B1/de not_active Expired - Lifetime
- 1986-06-02 HU HU863197A patent/HU204574B/hu not_active IP Right Cessation
- 1986-06-02 JP JP61503177A patent/JPH088876B2/ja not_active Expired - Fee Related
- 1986-06-06 DD DD86291082A patent/DD249041A5/de not_active IP Right Cessation
- 1986-06-10 CS CS864269A patent/CS258482B2/cs not_active IP Right Cessation
-
1994
- 1994-06-28 US US08/266,442 patent/US5516649A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HUT42136A (en) | 1987-06-29 |
| DE3521111A1 (de) | 1986-12-11 |
| JPS63500841A (ja) | 1988-03-31 |
| DE3671246D1 (de) | 1990-06-21 |
| CS258482B2 (en) | 1988-08-16 |
| EP0225892B1 (de) | 1990-05-16 |
| WO1986007385A1 (en) | 1986-12-18 |
| HU204574B (en) | 1992-01-28 |
| US5516649A (en) | 1996-05-14 |
| CS426986A2 (en) | 1987-12-17 |
| JPH088876B2 (ja) | 1996-01-31 |
| EP0225892A1 (de) | 1987-06-24 |
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